LOL, ya OK. Coming from a guy who writes novels on the side and never misspells anything
You wordsmith, you.
My thoughts on the pop-up since JohnR covered it well. Knowing Tracie a little and the fact she has never camped, I would recommend you try to find an enclosed unit over a popup. The first impressions are going to seal/break the deal and the creature comforts are just not there for someone who is not already used/comfortable with camping. Setup/tear down is much easier with an enclosed unit and having a bathroom is a HUGE plus for the ladies. Sure pop-ups come with toilets, but the privacy that women seek is not there. While sleeping, you can hear everything just like a tent through the canvas. Your neighbors, the entire campground, the rain, the thunder, etc. Everything you do inside of the camper will also be heard by your neighbors. Dropping a deuce, correcting Ms. K., arguing or loving the Mrs., etc. Most don't leak, but they also don't last as long as an enclosed unit unless the owner is someone who goes the extra mile to make sure it's dried out before storing. Mold, musty smells and the fear of the darn roof coming down gets old. I have never owned one, but spent many of nights in older ones through brand new ones. The new pop-ups are sweet, but they are well outside of your price range. Note - any camper you buy for $2500 is going to be 15+yrs old needing a higher level of maintenance. Or, it has had a leak or another issue that the seller most likely will not reveal. Or, it is not going to be over 12' long and now a bathroom and room to be comfortable is not going to be there. What I meant by risk in the earlier post is it's a balance. Anything cheap could give you unforeseen, big headache type of issues. Anything cheap is most likely not going to be easy/fast to sell should you decide it's not for the family then it becomes an argument issue if you're trying to get the $ out of it. You will never hear the end of it.
Don't think you need to buy from a dealer either. It's completely different than the automotive market. They are not loyal to their customers and Jayco has an industry leading, whopping, 2yr warranty. If it gives you peace of mind that is has had the major mechanicals gone over, then do it. Just like anything else, private owners are not going to know or tell you everything about the unit. You will have to go through it top to bottom.
You are comfortable pulling trailers. You will have a full size truck. Set a budget, stick to it, and figure out what falls in the sweet spot. Plenty of guys here that provide input, just start posting the ones you are looking at and we'll chime in. If you are set on paying cash only, then talk it over with her to see if you forego 1-2 beach trips. Just keep in mind if you need some leverage in the tax arena, interest is deductible as a second dwelling as long as it has a bathroom and sleeping areas.